When we arrived for dinner at Via Carota last week and noticed that our companion had complemented her Dior dress with an elegant black silk mask, we realized that it was high time to step up our game. The new collection for Alice + Olivia from Air Mail contributor Donald Robertson (or Drawbertson) is an ideal place to start. The styles, each decorated with an original illustration, are intended to start conversation. One hundred percent of the proceeds will be donated to the C.F.D.A.’s Diversity, Equity & Inclusion initiative, which helps Black creatives and professionals in the American fashion industry. ($15, aliceandolivia.com)

If anything can fill our cold hearts with joy, it’s finding the Perfect Everyday Skirt ™. Thank you, Victoria Beckham, for the spot-on tailoring of this high-rise, navy twill midi, finished with smart buttons in a nod to utilitarianism. Flattering, functional, and a little bit fun? Check, check, check. Beautifully suited for blouses, jackets, and sweaters alike, it’s the kind of thing that you’ll end up wearing at least twice a week, whether you intend to or not. ($790, matchesfashion.com)

Upon seeing this satin maxi-dress, with both the belt and trim in black with a subtle border of crystals, we couldn’t help but gasp, “Bacall!” It conjures better, more elegant days, straight out of How to Marry a Millionaire. Philosophy di Lorenzo Serafini specializes in this type of high-drama yet tasteful dressing, and between the relaxed silhouette and the long sleeves—all the better for staving off the season’s chill—this makes for an ideal ensemble for holiday gatherings both indoors and out. ($1,775; modaoperandi.com)

There are few things that transform a look from slipshod to polished quite like a belt. And yet they are chronically under-appreciated, too often overlooked by designers. Luckily for us, Isabel Marant understands their importance. We’re especially loving this looped style, which fastens easily but looks sufficiently déshabillé and compliqué to be interesting. Trousers of all varieties—including jeans—will receive an instant upgrade, while psychically transitioning you from “barely awake” to “fully dressed.” ($125, farfetch.com)